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Volumn 61, Issue 14, 1996, Pages 4634-4640

A tandem Horner-Emmons olefination-gonjugate addition approach to the synthesis of 1,5-Disubstituted-6-azabicyclo[3.2.1]octanes based on the AE ring structure of the norditerpenoid alkaloid methyllycaconitine

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EID: 0001732459     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9519672     Document Type: Article
Times cited : (25)

References (44)
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    • For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
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    • For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
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  • 4
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    • For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
    • (1992) J. Org. Chem. , vol.57 , pp. 3528
    • Jung, M.E.1    Longmei, Z.2    Tangsheng, P.3    Huiyan, Z.4    Yan, L.5    Jingyu, S.6
  • 5
    • 0000948339 scopus 로고
    • For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
    • (1984) J. Org. Chem. , vol.49 , pp. 2948
    • Petersen, J.S.1    Toteberg-Kaulen, S.2    Rapoport, H.3
  • 6
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    • For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 5085
    • Fevig, J.M.1    Marquis, R.W.2    Overman, L.E.3
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    • For a previous synthesis of a 1,5-dicyano-substituted azabicyclo-[3.2.1]octane see: Betts, B. E.; Davey, W. J. Chem. Soc. 1961, 1683.
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    • note
    • At a concentration of 16 mmol, Birch reduction of pyridine 8 with lithium and water, formed the required trisubstituted cyclohex-2-en-1-one 10 and the unrequired tetrasubstituted cyclohex-2-en-1-one (9) in 27% and 20% yields, respectively. With higher concentrations, diminished yields of 9 and 10 were obtained. (Equation Presented)
  • 30
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    • 5-Exo-trigonal ring closure of an amide NH group onto a ketone culminating in the formation of 6-methoxy-7-azabicyclo[4.2.1]nona-8-one has been reported, see: Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051.
    • (1972) Tetrahedron , vol.28 , pp. 4051
    • Newman, H.1    Fields, T.L.2
  • 31
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    • For previous syntheses of (6) see: (a) Cohen, T.; Yu, L. C. J. Am. Chem. Soc. 1983, 105, 2811. (b) Luzzio, F. A.; Moore, W. J. J. Org. Chem. 1993, 58, 2966.
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    • Cohen, T.1    Yu, L.C.2
  • 32
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    • For previous syntheses of (6) see: (a) Cohen, T.; Yu, L. C. J. Am. Chem. Soc. 1983, 105, 2811. (b) Luzzio, F. A.; Moore, W. J. J. Org. Chem. 1993, 58, 2966.
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    • Luzzio, F.A.1    Moore, W.J.2
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    • Olefination conjugate additions with phosphonate sulfones to optically active tetrahydropyrans have been described: (a) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B. Tetrahedron, Lett. 1988, 29, 693. (b) Keck, G. E.; Kachensky, D. F.; Enholm, E. J, J. Org. Chem. 1985, 50, 4317. (c) Bloch, R.; Seck, M. Tetrahedron 1989, 45, 3731. (d) Ali, M. H.; Hough, L.; Richardson, A. C. J. Chem. Soc., Chem. Commun. 1984, 447. (e) Georges, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 5754.
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    • Davidson, A.H.1    Hughes, L.R.2    Qureshi, S.S.3    Wright, B.4
  • 36
    • 0000590706 scopus 로고
    • Olefination conjugate additions with phosphonate sulfones to optically active tetrahydropyrans have been described: (a) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B. Tetrahedron, Lett. 1988, 29, 693. (b) Keck, G. E.; Kachensky, D. F.; Enholm, E. J, J. Org. Chem. 1985, 50, 4317. (c) Bloch, R.; Seck, M. Tetrahedron 1989, 45, 3731. (d) Ali, M. H.; Hough, L.; Richardson, A. C. J. Chem. Soc., Chem. Commun. 1984, 447. (e) Georges, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 5754.
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    • Keck, G.E.1    Kachensky, D.F.2    Enholm, E.J.3
  • 37
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    • Olefination conjugate additions with phosphonate sulfones to optically active tetrahydropyrans have been described: (a) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B. Tetrahedron, Lett. 1988, 29, 693. (b) Keck, G. E.; Kachensky, D. F.; Enholm, E. J, J. Org. Chem. 1985, 50, 4317. (c) Bloch, R.; Seck, M. Tetrahedron 1989, 45, 3731. (d) Ali, M. H.; Hough, L.; Richardson, A. C. J. Chem. Soc., Chem. Commun. 1984, 447. (e) Georges, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 5754.
    • (1989) Tetrahedron , vol.45 , pp. 3731
    • Bloch, R.1    Seck, M.2
  • 38
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    • Olefination conjugate additions with phosphonate sulfones to optically active tetrahydropyrans have been described: (a) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B. Tetrahedron, Lett. 1988, 29, 693. (b) Keck, G. E.; Kachensky, D. F.; Enholm, E. J, J. Org. Chem. 1985, 50, 4317. (c) Bloch, R.; Seck, M. Tetrahedron 1989, 45, 3731. (d) Ali, M. H.; Hough, L.; Richardson, A. C. J. Chem. Soc., Chem. Commun. 1984, 447. (e) Georges, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 5754.
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    • Ali, M.H.1    Hough, L.2    Richardson, A.C.3
  • 39
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    • Olefination conjugate additions with phosphonate sulfones to optically active tetrahydropyrans have been described: (a) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B. Tetrahedron, Lett. 1988, 29, 693. (b) Keck, G. E.; Kachensky, D. F.; Enholm, E. J, J. Org. Chem. 1985, 50, 4317. (c) Bloch, R.; Seck, M. Tetrahedron 1989, 45, 3731. (d) Ali, M. H.; Hough, L.; Richardson, A. C. J. Chem. Soc., Chem. Commun. 1984, 447. (e) Georges, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 5754.
    • (1985) J. Org. Chem. , vol.50 , pp. 5754
    • Georges, M.1    Fraser-Reid, B.2


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